Concise Synthesis of Isocoumarin-3-carboxylic Acid Esters

A concise synthesis of isocoumarin-3-carboxylic acid ester derivatives has been developed by a Pd catalyzed one-pot fluorocarbonylation/lactonization/β-elimination cascade reaction starting from easily prepared hydroxyesters. ortho-Bromobenzaldehyde derivatives were converted to 2-chloro-1-hydroxy-2...

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Bibliographic Details
Published in:Chemistry letters 2023-08, Vol.52 (8), p.640-643
Main Authors: Nakayama, Atsushi, Hamamoto, Ken-ichiro, Fujiwara, Ibuki, Fukuda, Eigo, Ozawa, Keita, Endo, Seiya, Yamasaki, Rika, Yamanaka, Hidemitsu, Tamura, Yusaku, Yamamoto, Yuki, Shinada, Tetsuro
Format: Article
Language:English
Subjects:
Carboxylic acids
Cascade chemical reactions
Esters
Synthesis
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Summary:A concise synthesis of isocoumarin-3-carboxylic acid ester derivatives has been developed by a Pd catalyzed one-pot fluorocarbonylation/lactonization/β-elimination cascade reaction starting from easily prepared hydroxyesters. ortho-Bromobenzaldehyde derivatives were converted to 2-chloro-1-hydroxy-2-arylpropionic acid esters in two steps via Darzens condensation. The resulting 1-hydroxypropionates were smoothly converted to isocoumarin-3-carboxylic acid esters in good yields by the newly developed cascade reaction in an efficient manner. The synthetic utility was demonstrated by the first total synthesis of penicipyran C.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.230219